Episode Promotional Offer: Mile 40 Listeners receive 40% off a first coaching session with Bishoy. Send an email to bishoy@bishoytadraos.com and use the subject "My Comeback Story" to claim the offer. Welcome to Episode 198 of the Mile 40 Podcast! Today Bishoy sits down with Deanna First, a New York based live illustrator who has spent the last decade drawing guests at the Met Gala, fashion weeks, movie premieres, and VIP suites across the city, for a conversation about what it actually takes to build a creative career with no roadmap, no connections, and no safety net. Deanna traces her path from a childhood in Cleveland, Ohio, the daughter of two teachers, to bouncing between apartments across New York while working side jobs to support herself as an artist. She opens up about the early rejections, the agency that booked her contacts instead of her, and the moment a simple Instagram reshare led to her first paid commission and a seat at a launch dinner next to Selena Gomez. Along the way, she reflects on her own intuition, her spirituality, and what it means to build a business and an identity that refuses to follow a script. The conversation also covers the tension between chaos and stability, how Deanna's relationship with money and self-worth evolved as her career grew, and how she has learned to say no to opportunities that do not serve her, even as her business, her family, and her sense of purpose continue to expand. What We Cover: Growing up the creative outlier in a family of teachersLeaving a corporate design job at Ralph Lauren and J.Crew to pursue illustration full timeThe Craigslist post and Instagram reshare that led to her first paid commissionWhat it actually means to work as a live illustratorGetting rejected by illustration agencies and learning to price her own workTelling her family she was leaving a traditional career pathSpirituality, intuition, and the isolation that can come with being an artistEmbracing chaos as a source of clarity rather than something to fearBalancing an unpredictable creative career with relationships and, now, a young family Deanna First is a New York City–based fashion and lifestyle illustrator known for her elegant, fluid illustrations and live sketching at high-profile events. Her work focuses heavily on movement, fashion, beauty, and capturing the personality and “aura” of her subjects within minutes. She earned a BFA in Fashion Design from Kent State University, which helped give her a strong understanding of fabric, movement, and how clothing falls and drapes. After college, she worked in fashion at Ralph Lauren, Elie Tahari, and J.Crew before ultimately leaving the fashion industry to pursue illustration full-time. What started as a childhood dream—she says she knew she wanted to be an artist as early as preschool—eventually became a 15-year career, including roughly a decade as a full-time artist Today, First works with major luxury and fashion brands including Chanel, Dior, Louis Vuitton, Tiffany & Co., Valentino, Bulgari, Christian Louboutin, Ralph Lauren, Bergdorf Goodman, Saks Fifth Avenue, and the Ritz-Carlton Yacht Collection, among others. Her work has also appeared in publications including Vogue and Forbes. More on Mile 40: https:mile40podcast.com/ Instagram: @mile40podcast @bishoy_tadros YouTube: https://www.youtube.com/@BishoyTadros
